Skyrim wasn't really designed for characters to hit the level cap. You have the option to do so if you want, but you can easily explore what the game has to offer even in none of your characters ever get past lvl 50.
How far you get level-wise also largely depends on your build. For example, my archer/assassin build is at level 61 and will stop leveling at 63 or 64.
I didn't specifically build her to level that far, but my skill choices just happened to bring her into that level range.
In case you're wondering:
- Primary skills: Archery, 1-Handed for backstabs, Illusion, Sneak, Alchemy
- Secondary: Smithing, Light Armor, Restoration, Pickpocketing
Skills that level in any case: Lockpicking, Speech, and sometimes Blocking